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Synthesis 1995; 1995(7): 851-854
DOI: 10.1055/s-1995-3999
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Dichlorophosphorylation of Adamantanols and 1-Adamantylcarbinols in Trifluoroacetic Acid

Elena V. Erokhina, Elvira A. Shokova, Yuri N. Luzikov, Vladimir V. Kovalev*
  • *Department of Chemistry, Lomonosov Moscow State University, Moscow, 111899 Russia, Fax +7(095)2335590; E-mail chesnok@ilsan.igem.msk.su
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Publication Date:
31 December 2000 (online)

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A convenient method for dichlorophosphorylation of adamantanols and 1-adamantyl alcohols with phosphorus trichloride in trifluoroacetic acid is described. The dichlorophosphoryl group is selectively introduced to the different positions of the adamantane nucleus as well as to the α-position of the side chain. The dichlorophosphorylation of 1-adamantylmethanol is found to be accompanied by adamantane-homoadamantane rearrangement leading to 3-homoadamantylphosphonic dichloride in 70% yield.

dichlorophosphorylation - trifluoroacetic acid - 1(2)-adamantyl-, 1-adamantylalkyl- and 3-homoadamantyl-phosphonic dichlorides